Although she didn’t start in pole position, Nancy Giacolone has come to lead the pack through determination, innovation and a client-centered approach.
By Scott Wooldridge // Photography by Tom McKenzie
Overcoming early roadblocks
In 1986, she parted ways with the agency where she worked and set off to start her own. Although Olympic Crest Insurance eventually developed a reputation for working with small businesses, at first Giacolone just wanted to be her own boss and create an agency that fit her personality. “That first year, I didn’t really know what I was doing,” she says. “Over time, my vision has really crystalized when it comes to providing employers and employees with information about their health plan and presenting it in a way that they can understand.”
Changes in the benefits landscape also played a role in the evolution of her firm and its growing focus on smaller businesses. “It was the advent of the Affordable Care Act that really triggered my need to stand up for small businesses,” she says. “Most large agencies and many smaller agencies began divesting themselves of small business clients, selling them off to service centers because they were afraid that they weren’t going to be able to generate enough profit from that segment.”
Nancy Giacolone has a need for speed.
Design by Chris Nicholls
The 2023 BenefitsPRO Broker of the Year is a big fan of fast cars. “I love everything about them,” she says. “If it goes fast, I want to be in it.”
As a young woman, she even raced cars. In fact, she met her husband, Jim, at a car event. “In 1985, my husband had a big block Corvette that he was showing; I convinced him to race it. That’s how we met.”
That fast pace is a part of everything Giacolone does, from running her brokerage, to meeting with clients and attending industry events, to creating informational videos and maintaining her strong social media presence. “Every day is a little different,” she says. “That’s one thing I like about this industry—if it were the same thing every day, I’d probably lose my mind.”
Giacolone works with a wide range of clients, but her Gig Harbor, Washington-based firm, Olympic Crest Insurance, has built a reputation for helping small business owners. “We’re a boutique benefits consulting firm and have been around for 27 years,” she says. “I do a lot of work with small businesses, but more than anything else, I’m an advocate for them. I feel very strongly that it’s an underrepresented market, so helping them and championing their cause makes up a large part of my business and philosophy.”
Nancy and her husband moved to Tacoma in 1985, where she found work as an administrative assistant in a local brokerage. She had a background in sales, and thought the insurance industry could become a career. “I liked it and was intrigued by it,” she says. “So I asked the people I worked for if I could get into sales.” The reception was not what she expected; the male sales staff at the firm told her she’d be terrible at it.“
This was the ‘80s,” she notes, when the benefits industry was still overwhelmingly made up of men. Not willing to take no for an answer, she worked out a deal with her employer: She would take a cut in pay and still work in administration half time. “I did that, and I was successful and soon moved into a full-time producer role. From there, I was eventually given an opportunity to become a full-time partner.”
Giacolone saw a lot of bias against women in the benefits space during her early years. For example, she was regularly asked whose assistant she was. In the years since, things have improved in the industry, but not a lot. “There’s still a long way to go,” she says. “It remains a very white-male-dominated industry; there’s no doubt about it.”
Again, Giacolone was willing to swim against the tide to pursue her vision. “Every sales coach encouraged focusing on large clients, and it just rubbed me the wrong way. The majority of independent agencies are small businesses, and they would not want to be treated the way I saw many of them treating their small clients.”
Giacolone has seen firsthand just how complicated the insurance world can be for smaller employers. She notes that small businesses make up the vast majority of the U.S. economy, with 98% of employers having fewer than 100 employees and 92% having fewer than 50. Yet small business owners must somehow manage HR, accounting, compliance and a multitude of other complicated tasks—each area presenting daunting challenges of its own.
Because of those realities, Giacolone says her agency does not have a one-size-fits all approach to providing solutions for clients. She is willing to try new ideas or work with the big carriers, when it makes sense.
“We hear a lot about how a 5,000-life case saved millions of dollars and the consultant was able to implement new and exciting programs, but we don’t often hear (or quite frankly, care) about the broker with a group of 12 who was able to move the parts around in their fully insured plan to save money and improve benefits,” Giacolone notes. “I continue to champion for these employers to bring innovative solutions down market, while also understanding that ‘burning down the BUCAs’ is not a practical solution for all employers.”
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Design by Chris Nicholls
A social presence
Part of Giacolone’s success in helping smaller businesses involves maximizing the resources provided by online media platforms. TikTok, LinkedIn, blogs, YouTube, podcasts—she has become an expert in all of them, providing hours of useful information to clients and the public at large.
Her approach can include elaborate set ups involving cameras, sound, and lighting, or can be as simple as a six-panel comic strip.
“My son works for me and having his perspective has been extremely helpful,” Giacolone says. “We often talk about how different groups or generations of
people will be
most receptive
to receiving
information. With
his help we
created OCI Guy,
a ‘benefits superhero’ who starred in many comics helping people understand their benefits.”
Her latest production is a podcast called “Recipe for Success,” in which Giacolone interviews a range of successful business people about their “secret sauce” for succeeding in businesses. “I love to cook,” she says. “I was in the kitchen one weekend and realized that with everything you make, there’s always one key ingredient. I realized everyone has their own recipe for success. That’s what I like to talk to people about: What is your secret ingredient?”
The secret ingredient
A blend of generosity and grace
“I realized everyone has their own recipe for success. That’s what I like to talk to people about: What is your secret ingredient?”
The podcast is now in its third year and often requires a lot of work to find guests and plan interviews. But Giacolone says she doesn’t over-plan or over-think the process. “I do the podcast live; it can be a little crazy. But I like that it’s not overly produced. I like to be real; I think it makes me more relatable.”
She uses LinkedIn for industry and employer information, while turning to Facebook and Instagram for content that works better on a personal level and with plan members. Meanwhile, TikTok works best for focused, bite-sized communication pieces. “And everything lives on YouTube as an overall library of content and communication,” she says.
Getting comfortable with presenting information on social media takes some time, Giacolone notes. “It really is a challenge, and a lot of people give up too soon, because they put something up and people aren’t ‘liking’ it. When I started, I did it every single day, and I don’t think anyone looked at my posts. But it’s about being consistent and continuing to have a presence,” she says. “I’ve built up my TikTok and grown from zero to 3,500 followers. It’s about consistency and offering valuable information. You have to provide value, otherwise people don’t care what you have to say.”
There’s been a lot of discussion among the big players in the benefits industry about reaching different demographics through various mediums and approaches, but Giacolone believes the industry remains behind on delivering information in an effective way. “A lot of it is institutional thinking. They come up with an idea and then tell us how great it is, without asking us. They’re not thinking of the practicalities,” she says. “I always think about it this way: ‘How would I want to receive that information?
Does it make sense to me? Is it logical? Can I understand it?’ That’s why I use so many forms and channels of communication. Everybody’s going to consume information in a different way.”
can happen when you are true to yourself. She’ll help anybody; she’ll talk to anybody. I know a number of people to whom she’s gone out of her way to provide a little bit of guidance.
“There are a lot of brokers who are helpful, but she really takes the time to understand who the client is. She doesn’t just slap something on and say, ‘Here’s what you’re going to get,’” De Paoli says. She also uses a cooking metaphor. “There are some basic recipes in our business, but you may need to tweak the recipe for the client; she’s very good at working with the employer and asking them why it is that they want to accomplish something.”
De Paoli also admires Giacolone for her work with younger brokers who are just beginning to make their mark on the industry. “She mentors a number of younger agents and agency owners,” she says. “I think she is a remarkable example of taking your professional success and pouring it into other people.”
So, what is Giacolone’s recipe for success? She has succeeded by staying true to her values and standing up for the needs of her clients. “My core values are honesty, kindness, respect and accountability,” she says. “They are all really important to me and a part of everything I do. If something doesn’t meet that test, then I don’t want to do it.”
This approach sometimes means pushing back against the industry when it gets too comfortable or set in its ways. But Giacolone sees staying true to these values and practices as her way of leaving a legacy.
“I don’t have that many years left in this role,” she says. “When I leave, I want to be somebody who stood up for people and did the right thing. That often involves respectfully calling out situations that aren’t right, whether it’s with an insurance company or with a competitor. I will speak up, because there are often a lot of loud voices in this industry who say, ‘This is how it has to be done.’ I quite often say that if you choose to do business that way, more power to you. But you have to understand that it is not the right approach for everyone. Everybody is different, and you have to meet clients and employees where they are.”
In an industry that sometimes rewards conformity, Giacolone has found her own voice and been successful doing it. “When you do the right thing, the rewards follow,” she says. “It’s just that simple.”
Allison De Paoli, like Giacolone, is a broker who works with a lot of small business owners. She met Giacolone at an industry function a few years ago, and says she immediately saw a kindred spirit who did not put up with foolishness but still treated others with respect and generosity. “I think we share a similar aesthetic,” De Paoli says. “We both have a particular viewpoint that the role of the broker is to be useful and helpful and do the best that is possible for the group.”
De Paoli, founder of Altiqe Consulting, a San Antonio-based benefits consulting firm, also appreciates Giacolone’s ability to connect with people and understand where they are coming from. “She’s always good with follow-up, talking to people, answering questions,” she says. “I think she has shown an exemplary amount of grace, which is what
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